Before the Worst
by spinningxoxo93
Summary: Blair is junior in college when she meets Sam Winchester. This is a story about falling in love under all the wrong circumstances. It is about finding love with different people and answering the question "is there really one great love" B/S, B/D, B/OC
1. Chapter 1

Authors Note: This is supposed to be about Blair's life after she goes to college using the books ending, so this means she was never with Chuck. But when you read the story I would like you think of Cyrus as he is in the show, not the book.

I don't own Gossip Girl, Supernatural or any of the other characters I used from other shows.

Blair has finished her first year at Yale and it is everything she expected it to be, but nothing she wants. When she decides to transfer her sophomore year she looks into Stanford University. To her surprise she ended up enjoying California when she went to visit her family over break. Although Stanford is not part of the Holy Trinity (Harvard, Yale and Princeton) that makes up ivy league schools, it is still on the top of the list.

When her sophomore year starts she finds herself enjoying it more than she ever did with Yale and Constance. The people are much more down earth and accepting. Weather is not a problem considering that Stanford is in northern California. During the winter it is not as cold as New York City, instead it is cool usually in the mid 50s. She is relieved that is not hot all year round, constant heat would get to be unbearable.

She declares a major in United States History. Her intentions were to go to law school, but she no longer thinks that would be a perfect fit for her. To say that Harold and Cyrus were upset was an understatement, but they both were able to move past it, just hoping that she will be happy. She's not sure what she is going to do with her major yet, but she definitely doesn't want to go into teaching. She thinks that maybe she can work in D.C to help restore the rich history of the United States. She can not believe that she has decided to settle for anything less then a lawyer, but in a way she is not really settling. A lawyer was always her fathers dream and it is about time she does something for herself, even if it means having a low paying salary. She also knows that if it ever comes down to it she will always have her trust fund and her family's line of hotels that has dated back from before her father's birth. She always looked up to her father and his ability to continue in the hotel business all the while following his dream as a lawyer. She knows that her Uncle Ben has much to do with their continuing family success, but her father will always be here hero.

She instantly becomes friends with her roommate, Erin Sliver. Silver, the name that she goes by, grew up in Beverly Hills, were Blair's family now lives. This makes traveling back home less boring, now that they have companions. Silver has a dark brown hair that she usually cuts into a bob. She has a great fashion sense, although it is a little too edgy and rocker for Blair's liking. She has a great personality and is the type of person you can always count on, unlike a former blonde friend.

Blair also becomes great friends with Haley James. They met in psychology class where they learned that they had declared the same major. Blair made some other friends as well, but Silver, Haley and Blair made an inseparable trio. It was the kind of friendship Blair always wanted. It wasn't cut short because of one sleeping with the others boyfriend. It was a solid, pure and lasting friendship. Blair does admit that there were times when she shared this relationship with Serena, but it always seemed to end due to a certain boy.

It is her junior year when she meets Sam Winchester. He accidentally knocks over her coffee while trying to multitask. He immediately apologizes and buys her a new cup. She gets a brief back story of his life. He is studying to be a lawyer and is in his second year of college. His mother died when he was a baby and he no longer speaks to his father or brother due to a fight they had when he left for school. His dad didn't want him to go to school and was upset at Sam for not continuing with the family business, although he never mentions what the business is. His brother, who practically idolizes his father, also stopped talking to Sam, not wanting to upset his father.

They decide to make coffee a weekly thing. Blair finds Sam to be attractive. He looks like a typical jock with his tall figure and built muscles, but he is exactly the opposite. He happens to be a major book worm, always studying or doing research on his computer. She finds herself falling for him, but any ideas of them being a couple are quickly diminished when he introduces her to Jessica. He brings her to coffee about two months after they initially started. He introduced her as his girlfriend and Blair put on her best fake smile and hugged her. Blair was not sure whether she was upset because he had a girlfriend or the fact that over the past three months while she practically poured her heart out to him he forgot to mention that he was seeing someone.

Jessica leaves early to get to class and Sam eagerly asks for Blair's opinion, "So what did you think of her?"

"She seems great, she is pretty, has goals, she's amazing, I just wish you told me you were seeing someone"

"We haven't been dating this whole time. We became official about a week ago"

"So, it's just that for the past three months we have been talking to each other with practically no boundaries and what, you just forgot to mention that you were talking to someone?"

"I'm sorry, I guess that was unfair."

"Whatever, don't worry about it she seems nice. You should bring her more often."

Blair didn't actually think that Sam would agree, but he did. Jessica would join them for coffee every week unless she had class or prior engagements. With Jessica's arrival Sam and Blair's relationship changed. They only really saw each other once a week and know that Jessica was always their, Blair was never really able to open up to Sam anymore. She did still email him about her problems, but it wasn't the same as actually talking to someone. Despite Jessica's intrusion on Blair and Sam's friendship she was actually a really nice person. Blair began to mind her less and less and their were a few times where Jessica would even ask Blair for advice. On the rare occasion Blair would ask Jessica for advice, almost to return the favor of Jessica asking her.

Both Sam and Jessica were present at Blair's graduation which she was thankful for. Haley, Silver and Blair decided to hold a graduation party at their apartment which Sam attended without Jessica because she was visiting her family. Sometime during the party Blair escaped to the rooftop where she sat and began to look back on her life. Her thoughts were interrupted with Sam.

"What are you thinking about?"

"Nothing really, just reflecting on my past and thinking about my move to Washington."

"Right, the big move to nation's capital."

Blair laughs, "yes"

"You excited?"

"Yeah, but I will miss the place, my friends, you---"

"Don't worry we'll still talk," Sam says pulling Blair into hug.

They continued to talk for the next hour, really catching up with each other. It has been awhile since the two of them were really able to talk without Jessica. They promised to keep in touch and they did.

It was a couple of months after her move to D.C when she heard about Jessica's death. She was shocked at first and immediately called Sam. She flew back for the funeral service where she embraced Sam in a huge hug. It was at Jessica's funeral where she was finally able to meet Dean. It was only for a few brief seconds, but she was captivated by him. He was shorter then Sam, but was definitely built. He had a face to die for and his cold exterior made him even more attractive. Sam left with his brother shortly after the funeral and so did Blair. She and Sam continued to keep in touch, but after a couple of months he stopped responding to her texts, phone calls and emails. She eventually stopped, pushing his memory into the far back of her head.

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She was now 25 and engaged to Lucas Scott, who she met through Haley. They got married on July 21st in New York , because the city will always be her home. She had a small bridal party that consisted of Haley and Silver. Nathan Scott, Lucas' brother and Haley's boyfriend, was the best man. Mouth was the other groomsmen. A few of Blair's old friends attended the wedding, including Nate and Serena. Their love triangle was a long time and now that she found the man she wanted to spend the rest of her life with it she wanted two of her oldest friends to witness it.

She and Serena were never able to salvage their friendship, which was a shame, but some things you just can't control. Serena was currently engaged to Dan Humphrey and they were planning a winter wedding, which Blair planned to attend. Nate was divorced and was know one of New York City's eligible bachelors. He seemed lost and sad that his two great loves were moving on with out him. He was living off his trust fund in some penthouse where he had a new girlfriend every week. I guess some things never change. Blair actually pitied him, glad that she was no longer involved with the mess that was Nathanial Archibald.

While Blair walked down the aisle towards Lucas she did glance over looking for that one person. Although they haven't spoken since they were 22, she hoped that he would show up, that their friendship meant something. She wasn't surprised when she didn't see his face, so she made her way to the front of the alter and recited her vows to Lucas.

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She is 26 when Lucas is murdered. His murder is shortly followed with the miscarriage of her baby. She quickly falls into a depression.

It's been a week since the miscarriage and two since the murder. Her doorbell rings and she ignores it at first, but whoever is there is persistent. When she looks out the window to see who it is she is shocked to see Sam and his brother Dean. Dean is the same as she remembers, although she only saw him for a few seconds. Sam has changed though. He is much more muscular and looks a little more rough around the edges. She opens the door and embraces Sam in hug while her tears stream down her face. She is crying for the loss of Lucas, for the loss of her unborn baby and for what maybe the continuation of a friendship that was put on hold so long ago. She should have been upset for him cutting contact with her and maybe if they met under different circumstances she would have.

Dean tells her about their life as hunters and shares with her the true reason for her the recent losses in her life. It was ghost of some lady seeking revenge against her husband for killing her and her child. Sam doesn't say much, but he doesn't have to. This news explains so many questions Blair has been asking herself. It all makes sense now, the family business, Jessica's death, him leaving with his brother, cutting of communication with her. She feels sorry for him, for them both. They are around death everyday, that must be a hard life.

They find the ghost's body and salt and burn the bones. Blair doesn't know if things can go back to normal after this. She is now aware of the evils in the world, can she really sit by and do nothing to stop it?

The brothers leave and Sam promises to keep in touch. He doesn't keep his promise unless you consider an email a month keeping in touch.

A month after they leave Blair decides to start hunting by herself. She first studies the lore and contacts other hunters before she starts doing the physical stuff. 7 months after her hunting Sam barges into her Motel Room. He starts screaming at her, telling her that this isn't the life for her. She breaks down crying, explaining that after learning the truth about Lucas' death she couldn't go back to normal. Sam says he understands and he insists that she hunt with him and Dean for awhile. He wanted to ensure that she was safe.

Dean was against the idea at first, but he figured after everything that happened this was the least he could do. They leave her with simple tasks, usually doing the research, never letting her in on the actual hunt. She is annoyed at first, but finds their protective behavior comforting.

They were at bar one night and Dean and Blair both a got a little drunk. One thing led to another and they ended up spending the night with each other. Sam came back in at 12 only to find Blair and Dean with their limbs entwined. He went back outside and slept in the car. If he said he wasn't jealous after seeing Blair with his brother that would have been a lie. A part of him, even back at Stanford, always cared for her, but he didn't think she was interested and then his relationship with Jessica went to the next level. He assumed they weren't meant to be together, but he wished that he was the one in that bed, not Dean.

Blair and Dean both stopped drinking after that night and for awhile things were a little awkward. Blair went back to getting her own motel room like when she first started hunting with them (after awhile to save money they decided to share one). It was about two months after when Dean finally kissed Blair. He wasn't drunk or high, he kissed her because he wanted to be with her. They started sleeping around afterwards, but only during the day not wanting Sammy to find out, but he wasn't stupid. He saw the girl he loved slowly fall for her brother. They started going out to eat together and he would volunteer to stay back and do research with her sending Sammy out on his own. When things started to get serious they told Sam about what was going on. He pretended that he didn't know just like he pretended that it didn't bother him.

Dean and Blair began to stay in their own motel rooms, as if they were a married couple. It was nice, finally being able to be alone with Dean. She never thought that she would love again after Lucas, but Dean changed everything.

Although she loved spending time alone with Dean, she did miss the times when she shared a room with Sam. She missed the times before her and Dean happened and when she would crash on the bed with Sam and fall asleep next to him. She swore to herself that it was only because she and Sam were close friends, but deep down she knew that he was more then just a friend.

Blair couldn't shake the feeling that she lived this life before. Her relationships with Dean and Sam seemed so familiar, but she couldn't place it.

A year passed, Blair and Dean were still together, while Sam was still very much in love with Blair. He began to drink more often, coming back drunk with random girls. There were times where he would go on a hunt by himself for a few days, but Dean wouldn't allow Sam to go away by himself and neither would Blair.

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They were hunting a Wendigo, but they needed the help of Bobby. His car had broken down and Dean volunteered to drive and get him. He was going to meet Bobby in Kansas, help him his fix the car and head back to California. Sam had wanted to go instead, not wanting to be left in California with Blair, but he knew he wouldn't be able to fix the car.

Dean and Blair parted goodbyes and when he left she turned to Sam, "I guess it's just you and me"

"Yeah," Sam says taking a rather large sip from his flask.

A few hours later Blair is lugging Sam's drunken body back to the motel. This is wear she kisses him. Well actually it is wear he kisses her, but she doesn't stop him. It's a brief kiss, maybe lasting 10 seconds, but it releases feelings that have been hidden for a long time. She pulls away on the verge of tears and Sam begins to pour his heart out.

"I love you, I think I always have. I can't bear to see you with Dean, it tears me apart. I just, I need you. I want to be with you. I want you to need me."

"Sam," She wants to tell him that she loves him too, but she can't. Too much has happened. "You're drunk, you need some sleep."

The next morning when Sam wakes up he is hit with memory of last night. Blair asks him if he wants breakfast as if nothing happened. While eating Sam tells her that whatever he said last night, not admitting that he is fully aware of what he said, meant nothing. That it was just the alcohol talking, but they both know that it's not the truth. They also agree not to tell Dean about the words or the kiss. That kiss would kill him and if it wouldn't evolve into anything then he didn't need to know.

Blair knows that it wasn't just a kiss and she finally realizes why her relationships with Dean and Sam seem so familiar. The truth is Blair has played in a story similar to this, except as a different character. In this new story Dean is to Blair as Sam is to Serena while Blair is to Nate. She has gotten herself involved in yet another love triangle and this time she is not the person being ripped apart she is doing the ripping. She doesn't like this realization because it forces her to see the truth. This will not end well, just like it didn't end well for the first players. She will leave tonight only leaving behind letters because she knows she can't stay. She can't inflict the same pain that was once inflicted on her. She will not tear apart a friendship that used to be inseparable because she knows that pain that comes with that. It happened to her and Serena as a result of Nate and she would not let it happen to Dean and Sam. The only way to save them and herself is to walk away and never look back.

That night when Dean comes back she leaves a note. One for Dean and one for Sam.

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She catches the first flight to France where she stays with her dad for the next couple of months. She gets her life back on track and moves to Dublin where she meets Kevin. He is different from everyone she has ever loved. He is different from Nate, Lucas, Dean and Sam. He is sweet with his Irish brogue and adorable when he sings and plays the guitar. They date for a couple of years and at 33 she marries him. It is a much smaller wedding, only a few guests attend. She slowly starts to live the life she lost when she left with _them._ She did stay in contact with Silver and Haley, but she made a much bigger effort to talk to them on the phone and actually see them and their children. Serena, who now lives in the London with Dan, visits Blair more in Dublin quite often. They were able to rebuild their friendship, which Blair is grateful for. It is at the times when she and Serena meet up that she wonders about Dean and Sam. She thinks about if they are still traveling together and if they are happy. She knows that she broke both of their hearts with leaving, but in reality it saved them from much greater heartache. She would know from experience.

She is happy with Kevin, never regrets her decision. They have three children, one of them being adopted. They still find time to enjoy the simple pleasantries of life. Every once and awhile they leave the kids with Serena and they go on a short couples retreat. Although the live in Dublin, Blair makes a point to take her kids to the United States every year. They go over during the summer, starting with New York, then visiting Silver in Boston, Haley in Tree Hill and lastly her mother in California.

Her life has taken many turns, with the loss of Lucas, her miscarriage, her relationship with Dean, her friendship with Sam, even her high school love triangle with Serena and Nate, but she doesn't regret anything because each and every one of her experiences made her the person she is today, made it possible to find her life in Dublin with Kevin and her kids.

There are some nights where she dreams about Sam. She wonders if they could have ever worked. Maybe if Jessica never died and they realized they weren't meant for each other Blair would have been able to make her move on Sam. She wonders if she never slept with Dean, that maybe Sam would have shared his feelings with her sooner. What she does know is that things would have never worked out under the circumstances they were put in.


	2. Author's Note

Please review and let me know what you think? I was thinking of writing two more chapters, one to sum up Dean's ending and another to sum up Sam's. Please review and let me know


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